Practice Problems for Final Part 2 UPDATED

Practice Problems for Final Part 2 UPDATED - Practice...

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Practice Problem Set for Final Exam – Alkene/Alkyne Chemistry Chem 3a, Spring 2011 – Prof. Bertozzi 1. In class we learned about the hydrohalogenation reaction of alkenes, which proceeds via a carbocation intermediate and leads to Markovnikov addition of H–X across the alkene. Another type of hydrohalogenation, exemplified below, involves a free radical chain mechanism and leads to anti-Markovnikov addition of H-X across the alkene. In this reaction, di- tert -butylperoxide serves as an initiator; its weak O–O bond undergoes homolytic cleavage at high temperatures. Using the curved-arrow notation, provide a step-wise mechanism for this reaction that illustrates the initiation, propagation and termination phases of the process. Explain the regiochemical preference for the anti-Markovnikov product. 2. In reaction ( a ) below, the alcohol substrate undergoes alkene chlorination followed by cyclization to afford what is essentially the Markovnikov product. By contrast, in the related reaction (
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This note was uploaded on 09/07/2011 for the course CHEM 3A taught by Professor Fretchet during the Spring '08 term at University of California, Berkeley.

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Practice Problems for Final Part 2 UPDATED - Practice...

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